4-Hydroxy-bicyclo[3.2.1]octane-1-carboxylic acid → 8-(4-Hydroxy-bicyclo[3.2.1]oct-1-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

HRID 480125Notes

Reaction equation

HRID 480125 reaction equation
[OH:1][CH:2]1[CH:8]2[CH2:9][C:5]([C:10](O)=O)([CH2:6][CH2:7]2)[CH2:4][CH2:3]1.Cl.[NH2:14][C:15]1[C:16](=[O:29])[N:17]([CH2:26][CH2:27][CH3:28])[C:18](=[O:25])[N:19]([CH2:22][CH2:23][CH3:24])[C:20]=1[NH2:21]>>[OH:1][CH:2]1[CH:8]2[CH2:9][C:5]([C:10]3[NH:14][C:15]4[C:16](=[O:29])[N:17]([CH2:26][CH2:27][CH3:28])[C:18](=[O:25])[N:19]([CH2:22][CH2:23][CH3:24])[C:20]=4[N:21]=3)([CH2:6][CH2:7]2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 127294454-Hydroxy-bicyclo[3.2.1]octane-1-carboxylic acidHCID 187676182,4(1H,3H)-Pyrimidinedione, 5,6-diamino-1,3-dipropyl-, hydrochloride (1:1)

Product 1

HCID 99288368-(4-Hydroxy-bicyclo[3.2.1]oct-1-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dioneYield 44.9%

Procedure

Using the method described in Example 8, 4-hydroxy-bicyclo[3.2.1]octane-1-carboxylic acid (Kraus, W., et al. Liebigs Ann. Chem., 1981, 10, 1826) (0.50 mmol, 0.085 g) was reacted with 5,6-diamino-1,3-dipropyl-1H-pyrimidine-2,4-dione hydrochloride (0.50 mmol, 0.132 g) to provide the desired product (0.081 g, 44%).

Sources & evidence

ORD record
ord-5f4762a4b03449cda94401439a04dc6f
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

Loading…